Old Bennington Sites

Walking Tour

The walking tour begins at the Paradise Inn which began as the name of a restaurant that opened in downtown Bennington in 1927 by James Playotis, a Greek self made millionaire who as a teen immigrated to the U.S. from the island of Mitilini. Guests of his restaurant were Muhhammad Ali, Betty Ford, Anthony Hopkins, and Shirly MacLaine. The Paradise Restaurant successfully served guests for nearly 35 years until a fire destroyed the building and surroundings in the downtown area. Plyotis then in 1964 along with his brother-in-law, Peter Pappas, purchased several acres of land behind his home on the west end of Main Street, moved the 1901 house to the back of the property where it still stands today, built a new Paradise Restaurant in its place and added the first of the three existing building that now makes up the Paradise Inn still owned by the same family.


Old Bennington – Turn left onto Main Street (Route 9)

Before any settlers of European Decent appeared, the Bennington area was inhabited by Native Americans who lived and hunted here as ear;y as 5000BC

Mountains surrounded the area protecting the broad, flat valley. Rivers and streams abound and it is rich in wildlife, wood, stone, and minerals. There is also an abundance of rich soil for farming.

Charted in 1749, Bennington was settled in 1761. The area neighboring the Paradise Inn, now known as Old Bennington, was the first part of town to be developed. The Old First Church and the courthouse were two of the first structures in the area. The settlers first sustained activity was farming, but in 1762 small mills appeared using water to power their machinery. During the Industrial Revolution of the  19th century larger factories were built downhill to harness the energy of the abundant water sources. As time went by commerce, housing, and cultural activities clustered in the present downtown area; however, agriculture and manufacturing still remain key aspects of Bennington’s modern economy.

The Bennington Museum

          Open 10am to 5pm, Closed Wednesdays. The expansive galleries feature a wide range of exhibits focusing on local arts and industry, including early Vermont furniture, paintings, and glass. The museum also contains the worlds largest collections of both Grandma Moses’s paintings and Bennington Pottery. Look too for the celebrated 1925 luxury car, the Wasp, 16 of which were handcrafted right here in Bennington.

Old First Church Cemetery

The graveyard itself out dates the church building it is adjacent to. Founders of the town of Bennington, Revolutionary Wars soldiers, Vermont governors, and the revered poet Robert Frost were all buried here. Also, Ethan Allen, leader of the famed Green Mountain Boys, once had a home within the cemetery’s grounds.

Old First Church

Open Monday-Saturday 10am-12pm & 1pm-4pm, with services still offered Sunday mornings. First gathered in 1762 this church, now deemed “Vermont’s Colonial Shrine,” still stands as one of the first awe-inspiring examples of early colonial architecture. Much of the early history of Bennington and of Vermont took place within and around this meeting house.

Walloomsac Inn

The Walloomsac Inn was built in 1764, making it the oldest inn in Vermont. Over the years many famous people have stayed at the Walloomsac including Presidents Thomas Jefferson, Ruthford B. Hayes and Benjamin Harrison.

Village Lion Fountain

Originally a watering trough for horses was later converted to a fountain for pedestrian use.

Catamount Tavern

Marked now by a granite & copper statue placed here in 1896, the tavern was built in 1769 and burned down in 1871. It served as headquarters for the Green Mountain Boys while they plotted against the Yorkers and the British; Ethan Allen planned the capture of Fort Ticonderoga and John Stark prepared for his victory in the Battle of Bennington here.

The Old Academy

Built in 1821, the Old Academy was meant to be the finest building in the state. It has had a rich history first as a private school, then as a public one, and finally as Old Bennington’s Public Library.

Bennington Battle Monument

Open 9am-5pm daily. Built in the late 1880s, this monument is a dedication to the famous Battle of Bennington. It was at this location that the American colonists maintained a store of weapons and food which British General Burgoyne needed to sustain his troops. the British were unsuccessful in there attempt to raid the Bennington store and in during the battle lost many men causing them to be defeated at their next two encounters and surrender soon after.